Water → (3,5-Diamino-6-(2,3,5-trichlorophenyl)pyrazin-2-yl)methanol

Reaction equation

[CH:1]([C:3]1[N:4]=[C:5]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[C:12]=2[Cl:19])[C:6]([NH2:10])=[N:7][C:8]=1[NH2:9])=[O:2].[BH4-].[Na+].O>C(O)C>[OH:2][CH2:1][C:3]1[N:4]=[C:5]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[C:12]=2[Cl:19])[C:6]([NH2:10])=[N:7][C:8]=1[NH2:9]

Participants

Procedure

To a stirred solution of 5-Formyl-2,6-Diamino-3-(2,3,5-trichlorophenyl)pyrazine (0.198 g, 6.24×10−4 mole) in ethanol (100 ml) was added sodium borohydride (0.0359, 9.35×10−4 mole) at room temperature. The reaction was stirred at room temperature under nitrogen for 1 hr, water (1 ml) was added and the solution evaporated in vacuo. The residue was dissolved in ethyl acetate (200 ml), washed with brine, dried over magnesium sulphate, filtered and evaporated in vacuo. The product was purified by ‘flash chromatography’ using 11-40% ethyl acetate in cyclohexane as the eluent. Yield 0.104 g (52%), M.p. 185-186° C. N.m.r. (D6DMSO) δ: 4.32 (2H, d), 4.98 (1H, t), 5.56 (2H, s), 5.85 (2H, s), 7.30 (1H, d), 7.76 (1H, d).